Seconded. Or a Yamaha or Honda for even less. There are a lot of great bikes that aren't "crotch rockets". If you really want to ride as opposed to trying to look cool by the definition of middle aged suburbanites, you can get a lot more for your money. Plus, why drop that much cash if it's something you may decide you don't even enjoy. I see a ton of cruisers for sale with less than 4,000 miles on them.
Like Frank said in another thread the other day a lot of those v-twin Harley's and clones are over priced and underengineered. Additionally, with Harley specifically a lot of what you're paying for is the mark.
I honestly think I got a great first bike when I bought a Honda CB750 Nighthawk. There is nothing cool about that bike, but it's still fun, still plenty of power for a beginner, and dirt cheap. Now I'm ready to upgrade when I can, but the bike I want now would have been too much when I was just starting out. Additionally I highly recommend you take the MSF rider safety course before you even get a bike if it's an option for you. Check around, some dealerships offer it and if they don't usually they can point you in the direction of a community college in your area that does. Even though you've ridden before it's a good class for street riding, and in some states will get you out of having to pass a dmv riders examine to obtain your license.

Dude don't get a harley unless you look old school and look like a killing machine. Other wise you end up joining the ranks of middle aged men out there who then they're not pissing everyone off at the stop light revving their engine they're sitting around the table with each other saying 'I'll have a Samuel Adams as well'.

second on the training if you haven't ridden for a while - I read somewhere the biggest group for mtc accidents/fatal crashes is the newbie 'over 40's' who had a Honda step through when they were 16, then a wfe/kids/house/career, then decide they need to feed their inner biker so go out and get a bike.
I love motorcycles and riding, but the harsh reality is people in cars are sooooo fuuuuucking stuuuuuupid whne it comes to bikes, and many on bikes don't realize how quick it can all go wrong.
So, whatever you get, ride safe.

Get a midsize cheapie and let it take your learning lumps - then sink some coin into something nice that fits the kind of riding you want to do.

ps - i got my latest BMW for around $3900 (89 RT 1000cc) and have spent a grand total of maybe $200 on a starter. (excluding oil, filters and tires) probably have 10-15,000 miles on it in 2.5 years.
my previous '75 600/6 I got for $900 in Seattle, put over 60,000 mi without any mechanical. then I made the mistake of doing a complete overhaul/rebuild (it was up to 110,000 miles and smoking a bit, lot of wear and tear) and the bike burned in a garage fire before I put any major miles on it.

i think the honda shadow is in your price range. a good low seat and center of gravity to get back on the saddle on. i've been riding off-and-on for a few years now and am getting that soon for a reliable daily.